Jill Kelly with her husband Dr. Scott Kelly. Tampa Bay Magazine(WASHINGTON) -- The Florida woman whose report of harassing emails from Paula Broadwell ultimately led to the resignation of CIA director Gen. David Petraeus may be a "nice, rich, bored socialite," as one U.S. official described her, but she also pursued close ties to top military and intelligence officials, and with her husband and twin sister has endured recent financial and legal woes.

Jill Kelley, 37, is a Tampa socialite who volunteered her time to support the military, planned and hosted charitable events and forged tight friendships with top brass. Her sister Natalie Kwaham also became friendly with major players, including both Gen. Petraeus and Gen. John Allen, commander of the International Security Assistance Force in Afghanistan, who wrote letters on her behalf as she battled her ex-husband for custody of her son.

"We and our family have been friends with Gen. Petraeus and his family for over five years," Kelley said in a statement. "We respect his and his family's privacy and want the same for us and our three children."

Kelley and her husband Scott Kelley, the parents of three, are close friends with the Petraeus family. The families have spent the holidays together several times over the years and celebrated Christmas together last year, according to Petraeus' daughter Anne's personal blog.

"Our friends from Tampa (the twins Jill and Natalie, plus Jill's husband Scott and their three little girls, as well as Natalie's 2-year-old son John) were in town and came over for an afternoon feast and presents at our place," she wrote in the blog.

Kelley's social efforts on behalf of the military earned her the unpaid title of "honorary ambassador" to CENTCOM, the Defense Department's Central Command, which is based in Tampa at MacDill Air Force Base and has responsibility for directing operations in Iraq and Afghanistan. A U.S. official described Kelley as a "nice, bored, rich socialite" who drops "honorary" from her title and tells people she is an ambassador.

When Kelley reported harassing emails from an unknown source, the emails were traced to the account of Paula Broadwell, co-author of the Petraeus biography All In. Investigators are said to have found intimate emails in Broadwell's inbox that pointed to an intimate affair with Petraeus. Petraeus announced his resignation as CIA director on Friday.

Kelley has not been romantically linked to Petraeus, but her link to Gen. John Allen, commander of the International Security Assistance Force in Afghanistan, is now under investigation.

Allen is under investigation for alleged "inappropriate communications" with Kelley.

The FBI has uncovered "potentially inappropriate" emails between Allen and Kelly, according to a senior U.S. defense official who is traveling with Defense Secretary Leon Panetta. The department is reviewing between 20,000 and 30,000 documents connected to this matter, the official said. The email exchanges between Kelley and Allen took place from 2010 to 2012.

The U.S. official said the emails were "innocuous" and mostly about upcoming dinner parties and seeing him on TV. Allen denies he was involved in an affair, a Pentagon official said. An intermediary for Allen told ABC News that Allen and his wife are friends with Kelley and her husband and most of the emails were sent from Kelley to Allen's wife.

Kelley's family is standing by her and denying any untoward allegations and insinuations.

"It is a shock," Kelley's brother David Khawan told ABC News' Tampa affiliate WFTS. "We are just trying to find out where the pieces are falling right now."

"She is very dedicated to her husband and to her kids," he said. "So, something like this is really pretty much a fluke. So, for anybody to paint her as otherwise is completely wrong."

But Kelley and her husband Scott, a surgeon, have also had to grapple with financial problems. They have been sued at least nine times. Court records indicate that the Kelleys owe more than $2 million on an office building and face foreclosure.

Natalie Khawam, who now lives with her sister and brother-in-law in Tampa, is deeply in debt and filed for bankruptcy in Florida in April 2012. In a document filed to the Tampa Division of the U.S. Bankruptcy Court, Khawam listed her personal property which included six Chanel purses, a Cartier watch, and a trove of diamond jewelry valued at $50,000, including the watch. The items are in the possession of Khawam's ex-husband Grayson Wolfe, according to the court documents.

She has also been embroiled in a child custody battle with Wolfe. Petraeus and Allen both wrote letters to the court on Khawam's behalf.

In Sept. 2012, Petraeus wrote a letter to the District of Columbia Superior Court stating that he and his wife had known Khawam for about three years, getting to know her while serving in Tampa, and maintaining their friendship since then.

"We have seen a very loving relationship -- a Mother working hard to provide her son enjoyable, educational, and developmental experiences," Petraeus wrote, according to a copy of the letter posted on Scribd. "Natalie clearly dotes on her son and goes to great lengths -- and great expense -- to spend quality time with him."

Allen's letter to the court also painted a portrait of a loving and devoted mother who "places the needs of her son above her own."